Sulfuric Acid → 4-(Methylsulfonyl)phenol

HRID 2070231Notes

Reaction equation

HRID 2070231 reaction equation
C1[C:6]([C@H:7]([CH2:12][NH2:13])[CH2:8][C:9]([OH:11])=[O:10])=[CH:5][CH:4]=C(Cl)C=1.[C:15](=[O:18])([O-:17])[O-].[K+].[K+].[CH3:21][CH:22]([CH3:44])[C:23]([O:25][CH:26](OC([O:33][C:34]1[CH:39]=[CH:38][C:37]([S:40]([CH3:43])(=[O:42])=[O:41])=[CH:36][CH:35]=1)=O)[CH:27](C)C)=[O:24].S(=O)(=O)(O)O.[C:50](#N)C>COC(C)(C)C.O>[CH3:50][CH:5]([CH3:4])[CH2:6][C@H:7]([CH2:12][NH:13][C:15]([O:17][CH2:27][CH2:26][O:25][C:23](=[O:24])[CH:22]([CH3:44])[CH3:21])=[O:18])[CH2:8][C:9]([OH:11])=[O:10].[CH3:43][S:40]([C:37]1[CH:38]=[CH:39][C:34]([OH:33])=[CH:35][CH:36]=1)(=[O:41])=[O:42]

Participants

9

Reactant 5

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 44602ArbaclofenHCID 592705152-Methyl-1-[4-(methylsulfonyl)phenoxycarbonyloxy]propyl 2-methylpropanoate

Product 2

HCID 1233504-(Methylsulfonyl)phenolHCID 86640714(3S)-5-Methyl-3-({[(2-methylpropanoyloxy)ethoxy]carbonylamino}methyl)hexanoic Acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

R-Baclofen (2.13 g) and water (50 mL) were charged to a vessel at room temperature. Potassium carbonate (1.6 g) was added in one portion and the mixture was stirred at room temperature for 5 minutes. A solution of 2-methyl-1-[4-(methylsulfonyl)phenoxycarbonyloxy]propyl 2-methylpropanoate D6 (3.5 g) in acetonitrile (50 mL) was added. After 6 hours, tert-butyl methyl ether (50 mL) was added and the reaction mixture was cooled to 5-10° C. A 5% aqueous sulfuric acid was added to adjust the pH to approximately 3. The mixture was then warmed to room temperature and stirred for 10 minutes. The organic layer was washed with water (3×20 mL) and evaporated to provide the crude title compound as an orange oil with 4-(methylsulfonyl)phenol impurity.

Workup

  1. waitAfter 6 hours
  2. temperaturethe reaction mixture was cooled to 5-10° C
  3. temperatureThe mixture was then warmed to room temperature
  4. stirringstirred for 10 minutes
  5. washThe organic layer was washed with water (3×20 mL)
  6. customevaporated

Sources & evidence

ORD record
ord-037d556ae9d74d86ab682802c1ce4935
Source dataset
uspto-grants-2012_10
Patent number
US08299291B2

Reaction notes

Loading…